title: [New photoreactive N(4)-substituted dCTP analogues:synthesis, photochemical characteristics, and substrate properties in HIV-1 reverse transcriptase catalyzed DNA synthesis].
abstract: Photochemical characteristics and substrate properties of four newly synthesized dCTP analogues: N4-[2-(2-nitro-5-azidobenzoylamino)ethyl]-, N4-[2-(4-azidotetrafluorobenzylideneaminooxymethylcarbamoyl)ethyl] -, N4-[4-(4-azidotetrafluorobenzylideneaminooxy)butyloxy]-, and N4-[4-(4-azidotetrafluorobenzylidene hydrazinocarbonyl)butylcarbamoyl]-, and N4-[4-(4-azidotetrafluorobenzylideneaminooxy)butyloxy]-2'-de oxycytidine 5'-triphosphates as well as those of the earlier described N4-[2-(4-azidotetrafluorobenzoylamino)ethyl]- and 5-[E-3-(4-azidotetrafluorobenzoylamino)-1-propenyl)]-2'-deoxycytid ine 5'-triphosphates were compared. When being irradiated with UV light at a wavelength of 303-313 nm, the new analogues demonstrated greater than 10-fold higher photoactivity as compared with the old compounds. The first three new compounds were utilized by HIV-1 reverse transcriptase as dCTP and dTTP, while the last derivative was recognized only as dTTP. Once incorporated into the primer 3'-terminus, none of the analogues synthesized terminated further primer elongation with natural triphosphates.
authors.forename: I V
authors.initials: IV
authors.lastname: Safronov
authors.forename: N V
authors.initials: NV
authors.lastname: Shcherbik
authors.forename: S N
authors.initials: SN
authors.lastname: Khodyreva
authors.forename: V A
authors.initials: VA
authors.lastname: Vlasov
authors.forename: M I
authors.initials: MI
authors.lastname: Dobrikov
authors.forename: G V
authors.initials: GV
authors.lastname: Shishkin
authors.forename: O I
authors.initials: OI
authors.lastname: Lavrik
mesh_terms: D002384:Catalysis; D004247:DNA / Q000096:biosynthesis*; D017931:DNA Primers; D003845:Deoxycytosine Nucleotides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects; D054303:HIV Reverse Transcriptase / Q000378:metabolism*; D010777:Photochemistry; D013329:Structure-Activity Relationship; D013379:Substrate Specificity; D014466:Ultraviolet Rays
chemical_list: D017931:DNA Primers; D003845:Deoxycytosine Nucleotides; C024107:2'-deoxycytidine 5'-triphosphate; D004247:DNA; D054303:HIV Reverse Transcriptase
vernacular_title: Novye fotoaktivnye N(4)-zameshchennye analogi dCTP: poluchenie, fiziko-khimicheskie i substratnye svoĭstva pri sinteze DNK, kataliziruemoĭ obratnoĭ transkriptazoĭ VICh-1.